Call to HttpSendRequestSync failed for port 443 with status code 404 Not Found

Today I was playing around in my lab environment with the goal to install a Management Point that would be used for HTTPS and have the ability to support Mac devices. I started with installing the prerequisites for a Management Point with my PowerShell script. After I’ve enrolled the ConfigMgr Web Server Certificate and the ConfigMgr Client Authentication Certificate, amended the Bindings on the Default Web Site in IIS, it all looked as it was working fine until the Management Point started throwing errors in the mpcontrol.log file as shown below:
Call to HttpSendRequestSync failed for port 443 with status code 404, text: Not Found
Here’s a more detailed view of the mpcontrol.log file on my Management Point Site server called
I first though that I got something wrong when I enrolled the certificates, and retraced my steps where I made sure I’ve put in the correct Alternative Subject Name DNS entries. Once I’ve enrolled new certificates, I restarted the SMS_EXECUTIVE service, but to my surprise, it still gave me the same error message. So I looked under Component Status for the SMS_COMPONENT_MONITOR on the server, and found the following:
So the Device Management Point was having problems, and was the component that actually was throwing the error in the mpcontrol.log file. I then went looking in the DMPSetup.log file located on my Management Point server under C:\SMS\Logs. There I could see that this component indeed had a rough time trying to install itself. On the second last row, I found the following:
Fatal MSI Error – dmp.msi could not be installed.
As for the mpcontrol.log file above, here’s the detailed view from the DMPSetup.log file:
This led me further into the world of ConfigMgr troubleshooting, on to the next log file. In this case it would be the dmpMSI.log.LastError present in the following location C:\SMS\Logs. Here I caught a bit of a break when I was searching for the last piece of information that had anything to do with the installation of this MSI file. It appeared that the MSI was dependent on the Web Server ASP.NET component. I determined that by simply reading the following line:
Product: ConfigMgr Device Management Point — ConfigMgr Device Management Point requires Web Server ASP.NET Component.
Could it really be that easy? Have I missed any of the Windows Features when I ran my PowerShell script to install the prerequisites? I opened an elevated PowerShell console and ran the following command:

Add-WindowsFeature -Name Web-ASP,Web-Asp-Net,Web-Asp-Net45

Once the features had been installed, I waited for the Device Management Point to try and reinstall itself. Once it did, the installation was successful and the error in mpcontrol.log disappeared.
Lesson learned from this was that you should always double check what features your script is installing, and if the correct ones.

Nickolaj Andersen

Chief Technical Architect and Enterprise Mobility MVP since 2016. Nickolaj has been in the IT industry for the past 10 years specializing in Enterprise Mobility and Security, Windows devices and deployments including automation. Awarded as PowerShell Hero in 2015 by the community for his script and tools contributions. Creator of ConfigMgr Prerequisites Tool, ConfigMgr OSD FrontEnd, ConfigMgr WebService to name a few. Frequent speaker at conferences such as Microsoft Ignite, NIC Conference and IT/Dev Connections including nordic user groups.

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